3-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridine → HCID 9946677, compound

HRID 586250Notes

Reaction equation

HRID 586250 reaction equation
Br[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][C:17]=1[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1>>[F:13][C:11]([C:9]1[CH:8]=[N:7][N:6]2[C:2]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[C:17]([C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[CH:18]=3)=[CH:3][N:4]=[C:5]2[N:10]=1)([F:14])[CH3:12]

Participants

3

Reactant 2

HCID 114265233-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridineHCID 22329502HCID 22329502, compound

Product 1

HCID 9946677HCID 9946677, compoundYield 44%

Procedure

This compound was prepared in 44% yield as described in the final paragraph of Example 2, step d, but using 7-bromo-3-(1,1-difluoroethyl)imidazo[1,2-b][1,2,4]triazine instead of 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine, and using 3-[2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine (prepared as described in Example 3, step f) instead of 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile: 1H NMR (360 MHz, CDCl3) δ 2.19 (3H, t, J 18.8 Hz), 7.36-7.47 (2H, m), 7.98 (1H, m), 8.08 (1H, m), 8.22 (1H, dd, J 2.3, 7.2 Hz), 8.45 (1H, s), 8.78 (1H, d, J 11.2 Hz), 8.85 (1H, s), 8.88 (1H, s); MS (ES+) m/z 356 [M+H]+. Anal. Found: C, 60.85; H, 3.45; N, 19.69%. Required for C18H12F3N5: C, 60.85; H, 3.40; N, 19.71%.

Workup

  1. customThis compound was prepared in 44% yield

Sources & evidence

ORD record
ord-5ad9753802d94fe4a2c822afec154c2c
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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